US4770807A - Novel extraction agents and novel propane diamides - Google Patents
Novel extraction agents and novel propane diamides Download PDFInfo
- Publication number
- US4770807A US4770807A US06/888,583 US88858386A US4770807A US 4770807 A US4770807 A US 4770807A US 88858386 A US88858386 A US 88858386A US 4770807 A US4770807 A US 4770807A
- Authority
- US
- United States
- Prior art keywords
- sub
- radical
- formula
- propane
- diamide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- -1 propane diamides Chemical class 0.000 title claims abstract description 90
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 23
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N dimethylmethane Natural products CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 title abstract description 27
- 239000001294 propane Substances 0.000 title abstract description 27
- 238000000605 extraction Methods 0.000 title description 46
- 150000003254 radicals Chemical class 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 15
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 239000003085 diluting agent Substances 0.000 claims description 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
- WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 claims description 6
- PQGAHNJECSVDEI-UHFFFAOYSA-N [CH2]CCCCC Chemical compound [CH2]CCCCC PQGAHNJECSVDEI-UHFFFAOYSA-N 0.000 claims description 3
- 125000006226 butoxyethyl group Chemical group 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 150000002602 lanthanoids Chemical class 0.000 abstract description 24
- 239000007864 aqueous solution Substances 0.000 abstract description 18
- 238000002360 preparation method Methods 0.000 abstract description 17
- 229910052768 actinide Inorganic materials 0.000 abstract description 15
- 150000001255 actinides Chemical class 0.000 abstract description 15
- 229910052747 lanthanoid Inorganic materials 0.000 abstract description 14
- 239000000243 solution Substances 0.000 abstract description 14
- 238000011084 recovery Methods 0.000 abstract description 12
- 239000002253 acid Substances 0.000 abstract description 6
- TVIBPFYUYRGOBB-UHFFFAOYSA-N n,n'-dibutyl-2-(2-ethoxyethyl)-n,n'-dimethylpropanediamide Chemical compound CCCCN(C)C(=O)C(CCOCC)C(=O)N(C)CCCC TVIBPFYUYRGOBB-UHFFFAOYSA-N 0.000 abstract description 6
- QZRKLYUPWNZTSW-UHFFFAOYSA-N n,n'-dibutyl-2-hexyl-n,n'-dimethylpropanediamide Chemical compound CCCCCCC(C(=O)N(C)CCCC)C(=O)N(C)CCCC QZRKLYUPWNZTSW-UHFFFAOYSA-N 0.000 abstract description 4
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 abstract 1
- 101150035983 str1 gene Proteins 0.000 abstract 1
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 48
- 239000012074 organic phase Substances 0.000 description 44
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 41
- LXQXZNRPTYVCNG-UHFFFAOYSA-N americium atom Chemical compound [Am] LXQXZNRPTYVCNG-UHFFFAOYSA-N 0.000 description 33
- 229910052695 Americium Inorganic materials 0.000 description 32
- 229910052693 Europium Inorganic materials 0.000 description 32
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 31
- WRIRWRKPLXCTFD-UHFFFAOYSA-N malonamide Chemical compound NC(=O)CC(N)=O WRIRWRKPLXCTFD-UHFFFAOYSA-N 0.000 description 30
- 238000000034 method Methods 0.000 description 24
- 230000008569 process Effects 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 239000008346 aqueous phase Substances 0.000 description 21
- 150000001875 compounds Chemical class 0.000 description 20
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 19
- 229910017604 nitric acid Inorganic materials 0.000 description 19
- 239000000203 mixture Substances 0.000 description 17
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
- 239000000047 product Substances 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 238000010586 diagram Methods 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 150000004820 halides Chemical class 0.000 description 8
- 150000002739 metals Chemical class 0.000 description 8
- MJMAULNTGHSPAS-UHFFFAOYSA-N n,n'-dibutyl-n,n'-dimethylpropanediamide Chemical compound CCCCN(C)C(=O)CC(=O)N(C)CCCC MJMAULNTGHSPAS-UHFFFAOYSA-N 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- ZPOLOEWJWXZUSP-WAYWQWQTSA-N bis(prop-2-enyl) (z)-but-2-enedioate Chemical compound C=CCOC(=O)\C=C/C(=O)OCC=C ZPOLOEWJWXZUSP-WAYWQWQTSA-N 0.000 description 7
- ZZZMLJZTGBZLFB-UHFFFAOYSA-N propanediamide Chemical group NC(=O)CC(N)=O.NC(=O)CC(N)=O ZZZMLJZTGBZLFB-UHFFFAOYSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 235000019647 acidic taste Nutrition 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- SXYFKXOFMCIXQW-UHFFFAOYSA-N propanedioyl dichloride Chemical compound ClC(=O)CC(Cl)=O SXYFKXOFMCIXQW-UHFFFAOYSA-N 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 238000001035 drying Methods 0.000 description 5
- UBGCCBQQNSSDHM-UHFFFAOYSA-N n,n'-dimethyl-n,n'-dioctylpropanediamide Chemical compound CCCCCCCCN(C)C(=O)CC(=O)N(C)CCCCCCCC UBGCCBQQNSSDHM-UHFFFAOYSA-N 0.000 description 5
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 150000001470 diamides Chemical class 0.000 description 4
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 4
- UKFXDFUAPNAMPJ-UHFFFAOYSA-N ethylmalonic acid Chemical group CCC(C(O)=O)C(O)=O UKFXDFUAPNAMPJ-UHFFFAOYSA-N 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000006263 metalation reaction Methods 0.000 description 4
- 239000010955 niobium Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
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- 230000015572 biosynthetic process Effects 0.000 description 3
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- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 238000004313 potentiometry Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- ANOOTOPTCJRUPK-UHFFFAOYSA-N 1-iodohexane Chemical compound CCCCCCI ANOOTOPTCJRUPK-UHFFFAOYSA-N 0.000 description 2
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical class OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
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- 150000003624 transition metals Chemical class 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- DNYWZCXLKNTFFI-UHFFFAOYSA-N uranium Chemical compound [U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U] DNYWZCXLKNTFFI-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01G—COMPOUNDS CONTAINING METALS NOT COVERED BY SUBCLASSES C01D OR C01F
- C01G56/00—Compounds of transuranic elements
- C01G56/001—Preparation involving a liquid-liquid extraction, an adsorption or an ion-exchange
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01F—COMPOUNDS OF THE METALS BERYLLIUM, MAGNESIUM, ALUMINIUM, CALCIUM, STRONTIUM, BARIUM, RADIUM, THORIUM, OR OF THE RARE-EARTH METALS
- C01F17/00—Compounds of rare earth metals
- C01F17/10—Preparation or treatment, e.g. separation or purification
- C01F17/17—Preparation or treatment, e.g. separation or purification involving a liquid-liquid extraction
-
- C—CHEMISTRY; METALLURGY
- C22—METALLURGY; FERROUS OR NON-FERROUS ALLOYS; TREATMENT OF ALLOYS OR NON-FERROUS METALS
- C22B—PRODUCTION AND REFINING OF METALS; PRETREATMENT OF RAW MATERIALS
- C22B3/00—Extraction of metal compounds from ores or concentrates by wet processes
- C22B3/20—Treatment or purification of solutions, e.g. obtained by leaching
- C22B3/26—Treatment or purification of solutions, e.g. obtained by leaching by liquid-liquid extraction using organic compounds
- C22B3/32—Carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C22—METALLURGY; FERROUS OR NON-FERROUS ALLOYS; TREATMENT OF ALLOYS OR NON-FERROUS METALS
- C22B—PRODUCTION AND REFINING OF METALS; PRETREATMENT OF RAW MATERIALS
- C22B60/00—Obtaining metals of atomic number 87 or higher, i.e. radioactive metals
- C22B60/02—Obtaining thorium, uranium, or other actinides
- C22B60/0204—Obtaining thorium, uranium, or other actinides obtaining uranium
- C22B60/0217—Obtaining thorium, uranium, or other actinides obtaining uranium by wet processes
- C22B60/0252—Obtaining thorium, uranium, or other actinides obtaining uranium by wet processes treatment or purification of solutions or of liquors or of slurries
- C22B60/026—Obtaining thorium, uranium, or other actinides obtaining uranium by wet processes treatment or purification of solutions or of liquors or of slurries liquid-liquid extraction with or without dissolution in organic solvents
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P10/00—Technologies related to metal processing
- Y02P10/20—Recycling
Definitions
- the present invention relates to the extraction of metals by means of extraction agents constituted by propane diamides and it more particularly applies to the recovery of actinides and/or lanthanides present in the trivalent state in an acid aqueous solution, particularly in a nitric solution.
- aqueous solutions of fission products are obtained, which contain relatively large quantities of trivalent ions of lanthanides and actinides.
- the effluents from these installations also contain the same ions.
- the present invention specifically relates to novel extraction agents more particularly usable for the recovery of actinides and/or lanthanides by extraction in an organic solvent containing at least one propane diamide, which obviates the aforementioned disadvantage and which also makes it possible to obtain improved extraction coefficients.
- novel extraction agents are constituted by a propane diamide of formula: ##STR3## in which R 1 and R 2 , which can be the same or different, represent a straight or branched alkyl radical having 1 to 15 carbon atoms or a radical of formula:
- R 4 is an alkyl radical with 1 to 6 carbon atoms
- n is equal to 0 or is an integer ranging between 1 and 6
- Z is a single bond or an oxygen atom
- m is an integer ranging between 1 and 6, provided that Z is a single bond when n is equal to 0 and R 3 represents a hydrogen atom, an alkyl radical with 1 to 15 carbon atoms, a radical of formula:
- n, m, Z and R 4 have the meanings given hereinbefore, or a radical of formula: ##STR4## in which R 1 and R 2 have the meanings given hereinbefore, provided that R 3 does not represent a hydrogen atom when R 1 and R 2 both represent an alkyl radical.
- These propane diamides can be used for recovering metals from generally acid aqueous solutions.
- These metals can belong to the group of transition metals, such as iron and zirconium, to the group of lanthanides or to the group of actinides.
- radical R 1 is a methyl radical.
- radicals R 2 and R 3 are a radical in accordance with formula:
- the propane diamide is in accordance with formula (I), in which R 1 is the methyl radical, R 2 an alkyl radical and R 3 the radical of formula:
- n, m, Z and R 4 have the meanings given hereinbefore.
- the substituents which can be used can comprise a single ether oxide function.
- n is equal to 0
- Z is a single bond and preferably m is equal to 1, 2 or 3, whilst R 4 is an alkyl radical with 2 to 6 carbon atoms.
- the substituents which can be used can also have two ether oxide functions.
- substituents in which n 2, Z represents an oxygen atom, m is equal to 2 and R 4 is an alkyl radical with 2 to 6 carbon atoms.
- the invention also relates to novel propane diamides according to formula: ##STR5## in which R 1 and R 2 , which can be the same or different, represent a straight or branched alkyl radical with 1 to 15 carbon atoms or a radical of formula:
- R 4 is an alkyl radical with 1 to 6 carbon atoms
- n is equal to 0, or is an integer ranging between 1 and 6
- Z is a single bond or an oxygen atom
- m is an integer ranging between 1 and 6, provided that Z is a single bond when n is equal to 0 and R 3 represents a hydrogen atom, an alkyl radical with 1 to 15 carbon atoms, or a radical of formula:
- n, m, Z and R 4 have the meanings given hereinbefore, provided that R 3 does not represent a hydrogen atom or an alkyl radical having 1 to 3 carbon atoms when R 1 and R 2 both represent an alkyl radical.
- At least one of the radicals R 1 , R 2 and R 3 complies with the formula:
- n, m, Z and R 4 have the meanings given hereinbefore.
- propane diamides When R 3 represents a hydrogen atom, tetrasubstituted propane diamides are obtained.
- propane diamides are N,N'-dimethyl-N,N'-dioctoxyethyl-propane diamide of formula: ##STR6## when R 3 differs from a hydrogen atom, pentasubstituted propane diamides are obtained.
- propane diamides examples include propane diamides of formula (I), in which R 1 is the methyl radical, R 2 the butyl radical and R 3 a radical chosen from among the ethoxyethyl, butoxyethyl, hexoxyethyl and hexoxyethoxyethyl radicals and the propane diamide for formula (I) in which R 1 is the methyl radical, R 2 the octyl radical and R 3 the hexoxyethyl radical.
- propane diamides are particularly interesting, because the presence of an ether oxide function on one of the substituents makes it possible to obtain improved properties for the extraction of actinides and lanthanides.
- the propane diamide can also be a propane diamide pentasubstituted by alkyl radicals.
- propane diamides in accordance with formula (I), in which R 1 is the methyl radical, R 2 the butyl radical and R 3 the butyl or hexyl radical.
- the propane diamides according to the invention can be in the form of a mixture of isomers or in the form of isomers. Furthermore, it is pointed out that the formulas given herein can either represent a mixture of isomers or one of the isomers.
- novel extraction agents based on pentasubstituted propane diamides can be prepared by a four stage process on the basis of an alkyl malonate.
- the radical of formula R 3 is fixed to the alkyl malonate by the reaction of the alkyl malonate with a halide of formula R 3 X in the presence of sodium, which corresponds to the following reaction diagram: ##STR7## in which R 5 represents an alkyl radical.
- the present invention also proposes a process for the preparation of pentasubstituted propane diamides making it possible to obviate this disadvantage.
- metallation agents e.g. n-butyl lithium or t-butyl lithium.
- the halides of formula R 3 X are preferably bromides or iodides and they can be prepared, when R 3 contains an ether group, by using the process described by F. C. Cooper and M. W. Partridge in J. Chem. Soc., 1950, p 459.
- a metallation reaction of the tetrasubstituted propane diamide e.g. by n or t-butyl lithium in accordance with the following reaction diagram: ##STR14## and then the halide of formula R 3 X is condensed on the product formed during the metallation reaction in accordance with the following reaction diagram: ##STR15##
- the tetrasubstituted propane diamides used as the starting product in the process according to the invention can be prepared by the amination of the malonyl chloride by means of corresponding amines of formula ##STR16## using the reaction described hereinbefore in the case of substituted malonyl chlorides.
- This reaction is generally performed in the presence of a catalyst, such as triethyl amine.
- a catalyst such as triethyl amine.
- the present invention proposes another process for the preparation of tetrasubstituted propane diamides making it possible to obtain good yields, even when the radicals R 1 and/or R 2 of the amine have more than 4 carbon atoms.
- preparation takes place of tetrasubstituted propane diamides of formula: ##STR17## in which R 1 and R 2 have the meanings given hereinbefore, by reacting an alkyl malonate of formula: ##STR18## in which R 5 represents an alkyl radical, with the corresponding amine of formula ##STR19## in the presence of a catalyst.
- the alkyl malonate is ethyl malonate and the reaction takes place in the presence of a catalyst such as hydroxypyridine, operating at a temperature above ambient temperature and e.g. at 140° to 170° C.
- the starting amines used for the preparation of the tetrasubstituted propane diamides and pentasubstituted propane diamides can be prepared by conventional processes, particularly that described by J. L. Nelson and RC. Sentz in J. Amer. Chem. Soc. vol. 74, p 1704, 1952.
- the inventive process for the preparation of pentasubsituted propane diamides thus has the advantage of making it possible to obtain such products in two stages from commercial products, such as ethyl malonate and the halide of formula R 3 X.
- the process according to the invention is advantageous because it places the critical branching stage, i.e. the introduction of radical R 3 , last, whereas it is performed first in the four stage synthesis process.
- R 1 and R 2 can be the same or different and represent a straight or branched alkyl radical with 1 to 15 carbon atoms or a radical of formula:
- R 4 is an alkyl radical with 1 to 6 carbon atoms
- n is equal to 0 or is an integer ranging between 1 and 6
- Z is a single bond or an oxygen atom
- the process consists of reacting a tetrasubstituted propane diamide of formula: ##STR22## in which R 1 and R 2 have the meanings given hereinbefore with a methoxyalkyl halide of formula XCH 2 OR, which X represents a halogen atom and R an alkyl radical with 1 to 8 carbon atoms, e.g. a methoxymethyl halide of formula XCH 2 --OCH 3 , in the presence of a metallation agent, such as n-butyl lithium or t-butyl lithium.
- a metallation agent such as n-butyl lithium or t-butyl lithium.
- the product obtained is constituted by a mixture of isomers.
- the extraction agent used can be one of three isomers or a mixture thereof and it is pointed out that the formulas given herein can either represent one of these isomers or the mixture of isomers obtained by the processes described hereinbefore.
- the invention more particularly applies to the recovery of actinides and/or lanthanides present in the trivalent state in an acid aqueous solution.
- the invention also relates to a process for the recovery of actinides and/or lanthanides present in the trivalent state in an acid aqueous solution, which consists of contacting said aqueous solution with an organic phase comprising at least one extraction agent chosen from among the extraction agents based on propane diamides according to formula (I).
- the organic phase used for extraction purposes generally comprises a diluent and the propane diamide concentration of the organic phase is preferably 0.1 to 1.5 mol.l -1 .
- the extraction rate generally increases with the propane diamide concentration of the organic phase.
- propane diamide contents not exceeding 1.5 mol.l -1 .
- the diluents which can be used are inert organic diluents preferably having a not very high dielectric constant.
- examples of such diluents are benzene, xylene, mesitylene, t-butyl benzene, dodecane and mixtures thereof.
- the diluent used is a mixture of decanol and a compound chosen from among benzene, xylene, mesitylene, t-butyl benzene and dodecane, because the presence of decanol makes it possible to avoid the formation of a third phase for low concentrations of lanthanides or actinides extracted in the organic phase.
- the organic phase generally comprises at the most 20% by volume of decanol.
- the process according to the invention can be used for recovering actinides and lanthanides from different aqueous solutions, but in particular nitric solutions.
- the process according to the invention can be performed in any conventional extraction apparatus, such as groups of mixer-settler means, pulsed columns, centrifugal extractors, etc. Generally, working takes place at ambient temperature and pressure with aqueous phase:organic phase volume ratios between 10:1 and 1:10.
- actinides (III) and lanthanides (III) extracted in the organic phase can then be recovered with very good yields by reextraction in water.
- FIGS. 1 and 2 Graphs showing the variations of the distribution coefficients D Am of americium and D Eu of europium, as a function of the nitric acid concentration of the aqueous solution to be treated, when using as the organic extractant 2-hexyl-N,N'-dimethyl-N,N'-dibutyl-propane diamide (FIG. 1) and 2-ethoxyethyl-N,N'-dimethyl-N,N'-dibutyl-propane diamide (FIG. 2), at concentrations of 0.5 mol.l -1 in a diluent of 90% t-butyl benzene and 10% decanol.
- FIGS. 1 and 2 Graphs showing the variations of the distribution coefficients D Am of americium and D Eu of europium, as a function of the nitric acid concentration of the aqueous solution to be treated, when using as the organic extractant 2-hexyl-N,N'-d
- FIGS. 3 and 4 Graphs showing the variations of the distribution coefficients D Am of americium and D Eu of europium as a function of the diamide concentration of the organic phase when using as the diamide 2-hexyl-N,N'-dimethyl-N,N'-dibutyl-propane diamide (FIG. 3) and 2-ethoxyethyl-N,N'-dimethyl-N,N'-dibutyl-propane diamide (FIG. 4) and a diluent of 90% t-butyl benzene and 10% decanol, the aqueous phase being 5N nitric acid.
- FIG. 5 A diagram showing the variations of the distribution coefficients D Am and D Eu as a function of the decanol concentration of the diluent of the organic phase.
- FIG. 6 A diagram showing the variations of the distribution coefficients D Am and D Eu , as a function of the nitric acid concentrations of the aqueous solution to be treated, when using as the extractant N,N'-dimethyl-N,N'-diethoxyoctyl propane diamide at a concentration of 0.5 mol.l -1 in t-butyl benzene.
- FIG. 7 A graph showing the variations of the distribution coefficients D Am and D Eu as a function of the nitric acid concentration of the aqueous solution to be treated, when using as the extractant (2-(3,6-OD)DBDMPDA.
- FIG. 8 A graph showing the variations of the distribution coefficients D U , D Pu , D Zr , D FE and D Nb as a function of the nitric acid concentration of the aqueous solution, when using as the extractant the propane diamide according to the invention constituted by compound 11.
- Examples 1 and 2 illustrate the preparation of tetrasubstituted propane diamides.
- Examples 3 to 7 illustrate the preparation of pentasubstituted propane diamides using the process according to the invention and the novel compounds obtained by this process.
- Examples 8 to 17 illustrate the use of the propane diamides according to the invention for the extraction of actinides and lanthanides.
- Cooling is followed by filtration, abundant washing with water to eliminate the triethylamine hydrochloride, drying the organic phase, expelling the solvent and distillation. In this way 97 g of a liquid is recovered, which distills at 140°-144° C. under 0.3 mm of mercury (40.5 Pa), which corresponds to a 40% yield.
- This product crystallizes in hexane at 5° C. (m.p. 51.5° C.).
- This product is characterized by nuclear magnetic resonance of the proton and by potentiometric dosing and it is established that it corresponds to the above formula.
- N,N'-dimethyl-N,N'-dibutyl-propane diamide was prepared and was then reacted by following the operating procedure of example 3(b) with butyl iodide. This gave 2-butyl-N,N'-dimethyl-N,N'-dibutyl-propane diamide with a yield of 47.6%.
- the pentasubstituted propane diamides were prepared (compounds 9 to 12 of table 2) by reacting the N,N'-dimethyl-N,N'-dibutyl-propane diamide obtained example 3 with the corresponding bromides in the case of compounds 9 to 11, or N,N'-dimethyl-N,N'-dioctyl-propane diamide obtained in example 1 with the corresponding alkyl bromide in the case of compound 12.
- This product was characterized by mass spectrometry, nuclear magnetic resonance of the proton and potentiometry.
- This example illustrates the recovery of americium and europium respectively present at concentrations of 10 -4 mol.l -1 for Am (III) and 10 -2 mol.l -1 for Eu (III) in nitric aqueous solutions of different acidities.
- curve 3 (in dotted line form) illustrates the results obtained with regards to the americium distribution coefficient, when extraction is carried out under the same conditions using the prior art N,N'-dimethyl-N,N'-dioctylpropane diamide.
- This example also relates to the extraction of the americium and europium respectively present at concentrations of 10 -4 mol.l -1 for Am (III) and 10 -2 mol.l -1 for Eu (III) in the nitric aqueous solutions of different acidities using propane diamide constituted by compound 8 obtained in example 5 (2-(3-OP)DBDMPDA).
- an organic phase constituted by the diamide obtained in example 5, i.e. 2-ethoxyethyl-N,N'-dimethyl-N,N'-dibutyl-propane diamide (2-(3-OP)DBDMPDA) at a concentration of 0.5 mol.l -1 in an organic phase having 90% by volume of t-butyl benzene and 10% by volume of decanol.
- Extraction of the europium and americium takes place under the same conditions as in example 8 and after 4 minutes contacting time, the americium and europium concentrations of the aqueous phase and organic phase are measured. The americium and europium distribution coefficients are then determined.
- the dotted line curve 6 relates to the results obtained under the same conditions for americium with the prior art N,N'-dimethyl-N-N'-dioctyl-propane diamide (DODMPDA). It is possible to see that the americium and europium distribution coefficient increases with the nitric acid concentration of the aqueous phase and that the best distribution coefficients are obtained for nitric acid concentrations of 5 to 6 mol.l -1 .
- DODMPDA N,N'-dimethyl-N-N'-dioctyl-propane diamide
- This example also relates to the recovery of the americium and europium present in the trivalent state in an aqueous nitric phase having a HNO 3 concentration of 5 mol.l -1 , Am (III) concentration of 10 -4 mol.l -1 and a Eu (III) concentration of 10 -2 mol.l -1 .
- Curve 9 relates to americium and curve 10 to europium. It can be seen that the distribution coefficients D Am and D Eu rapidly increase with the propane diamide concentration of the organic phase.
- This example relates to the recovery of americium (III) and europium (III) from an aqueous solution identical to that of examples 10 and 11.
- organic phases comprising either 0.5 mol.l -1 or 2-HDBDMPDA (compound 6) or 0,.5 mol.l -1 of 2-(3-OP) DBDMPDA (compound 8) in a mixture of t-butyl benzene and decanol with different t-butyl benzene and decanol ratios.
- Extraction takes place under the same conditions as in examples 10 and 11 and the distribution coefficients of americium and europium are determined after extraction. The results obtained are given in FIG. 5 showing the distribution coefficients of americium and europium as a function of the decanol volume percentage in the organic phase.
- Curve 11 relates to americium and to the propane diamide of example 5 (2-(3-OP)DBDMPDA
- curve 12 relates to americium and propane diamide of example 3
- curve 13 relates to europium and propane diamide of example 5 (2-(3-OP)DBDMPDA)
- curve 14 relates to europium and propane diamide of example 3 (2-HDBDMPDA).
- the organic phase is constituted by the propane diamide of example 3 (2l -HDBDMPDA) diluted either in pure t-butyl benzene at a concentration of 0.75 mol.l -1 , or in a mixture of t-butyl benzene and decanol containing 10% decanol or 20% decanol at a concentration of 0.625 mol.l -1 .
- the praseodymium nitrate is introduced into this organic phase until a third phase appears and the limit concentration corresponding to the appearance of said third phase is plotted.
- the results obtained are given in the attached table.
- This example illustrates the recovery of americium and europium respectively present at concentrations of 10 -4 mol.l for Am(III) and 10 -2 mol.l -1 and Eu(III) in nitric aqueous solutions of different acidities, by means of the propane diamide constituted by compound 5 (DIAM 802) of table 1.
- an organic phase constituted by propane diamide DIAM 802 of the table 1 at a concentration of 0.5 mol.l -1 in t-butyl benzene. Extraction takes place under the same conditions as in example 8 and after contacting for four minutes, the americium europium concentrations of the aqueous and organic phase are measured. The americium and europium distribution coefficients are then determined.
- the dotted line curves 17 and 18 illustrate the results obtained with respect to the distribution coefficient of americium (curve 17) and the distribution coefficient of europium (curve 18), when extraction is carried out under the same conditions using the prior art N,N'-dimethyl-N,N'-dioctyl-propane diamide.
- This example illustrates the recovery of americium and europium respectively present at concentrations of 10 -4 mol.l -1 for Am(III) and 10 -2 mol.l -1 for Eu(III) in nitric aqueous solutions of different acidities by means of the propane diamide constituted by compound 11 of table 2 of formula: ##STR31## hereinafter referred to as 2-(3,6-OD) DBDMPDA.
- This example illustrates the use of dipropane diamide constituted by compound 13 of example 7 for the extraction of americium (III) and europium (III).
- dipropane diamide constituted by compound 13 of example 7 for the extraction of americium (III) and europium (III).
- use is made of a 4N nitric acid solution containing americium and europium and an organic phase constituted by compound 13 at a concentration of 0.5 mol.l -1 in t-butyl benzene.
- This example illustrates the use of compound 11 of table 2 for the extraction of different metals such as U(VI), Pu(IV), Ar(IV), Fe(III) and Nb(V), from nitric solution containing 10 -2 mol.l -1 of said metals.
- Extraction takes place using aqueous phases of different acidities and an organic phase constituted by compound 11 of table 2 of example 6 at a concentration of 0.5 mol.l -1 in t-butyl benzene.
- Extraction takes place under the same conditions as those of example 8 and after 4 minutes contacting, measurement takes place of the metal concentrations of the aqueous and organic phases. The distribution coefficients of the different metals are then determined.
Abstract
Description
--(CH.sub.2).sub.n --Z--(CH.sub.2).sub.m --O--R.sup.4
--(CH.sub.2).sub.n --Z--(CH.sub.2).sub.m --O--R.sup.4
--(CH.sub.2).sub.n --Z--(CH.sub.2).sub.m --O--R.sup.4
--(CH.sub.2).sub.n --Z--(CH.sub.2).sub.m --O--R.sup.4
--(CH.sub.2).sub.n --Z--(CH.sub.2).sub.m --O--R.sup.4
--(CH.sub.2).sub.n --Z--(CH.sub.2).sub.m --O--R.sup.4
--(CH.sub.2).sub.n --Z--(CH.sub.2).sub.m OR.sup.4
--(CH.sub.2).sub.n --Z--(CH.sub.2).sub.m --O--R.sup.4
TABLE 1 ______________________________________ ##STR25## Compound No. R.sup.1 R.sup.2 Yield b.p. ______________________________________ 1(DIAM 8) CH.sub.3 C.sub.8 H.sub.17 52% 185-190° C./1 mm (135 Pa) 2(DIAM 6) CH.sub.3 C.sub.6 H.sub.13 30% 170-175° C./0.5 mm (67.5 Pa) 3(DIAM 4,8) C.sub.4 H.sub.9 C.sub.8 H.sub.17 25% -- 4(DIAM 4,4) C.sub.4 H.sub.9 C.sub.4 H.sub.9 47% 172-177° C./1 mm (135 Pa) 5(DIAM 802) CH.sub.3 C.sub.2 H.sub.4 OC.sub.8 H.sub.17 50% -- ______________________________________
TABLE 2 ______________________________________ Com- pound R.sup.1 R.sup.2 R.sup.3 Yield ______________________________________ No. 8 CH.sub.3 C.sub.4 H.sub.9 C.sub.2 H.sub.4 OC.sub.2 H.sub.5 40% No. 9 CH.sub.3 C.sub.4 H.sub.9 C.sub.2 H.sub.4 OC.sub.4 H.sub.9 52.7% No. 10 CH.sub.3 C.sub.4 H.sub.9 C.sub.2 H.sub.4 OC.sub.6 H.sub.13 55.6% No. 11 CH.sub.3 C.sub.4 H.sub.9 C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OC.sub.6 H.sub.13 40.5% No. 12 CH.sub.3 C.sub.8 H.sub.17 C.sub.2 H.sub.4 OC.sub.6 H.sub.13 51% No. 14 CH.sub.3 C.sub.4 H.sub.9 C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OC.sub.8 H.sub.17 60% No. 15 CH.sub.3 C.sub.4 H.sub.9 ##STR29## 55% ______________________________________
TABLE __________________________________________________________________________ Appearance of the % Saturation Extractant Diluant third phase of the solvent __________________________________________________________________________ 0.75 M 2-hexyl N,N'-- t-butylbenzene 0.075 M Pr(NO.sub.3).sub.3 20% dibutyldimethylpropane diamide (2-HDBDMPDA) 0.625 M 2-HDBDMPDA t-butylbenzene + 0.17 M Pr(NO.sub.3).sub.3 50% 10% decanol 0.625 M 2-HDBDMPDA t-butylbenzene + 0.218 M Pr(NO.sub.3).sub.3 70% 20% decanol __________________________________________________________________________
Claims (14)
--(CH.sub.2).sub.n --Z--(CH.sub.2).sub.m --O--R.sup.4
--(CH.sub.2).sub.n --Z--(CH.sub.2).sub.m --O--R.sup.4
--(CH.sub.2).sub.n --Z--(CH.sub.2).sub.m --O--R.sup.4
--(CH.sub.2).sub.n --Z--(CH.sub.2).sub.m --O--R.sup.4
--(CH.sub.2).sub.n --Z--(CH.sub.2).sub.m --O--R.sup.4
--(CH.sub.2).sub.n --Z--(CH.sub.2).sub.m --O--R.sup.4
--(CH.sub.2).sub.n --Z--(CH.sub.2).sub.m OR.sup.4
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR8511706 | 1985-07-31 | ||
FR8511706A FR2585700B1 (en) | 1985-07-31 | 1985-07-31 | NOVEL PROPANEDIAMIDES AND PROCESSES FOR THEIR PREPARATION |
FR8511707 | 1985-07-31 | ||
FR8511707A FR2585692B1 (en) | 1985-07-31 | 1985-07-31 | PROCESS FOR RECOVERING ACTINIDES AND / OR LANTHANIDES BY EXTRACTION IN AN ORGANIC SOLVENT CONTAINING A PROPANEDIAMIDE |
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US4770807A true US4770807A (en) | 1988-09-13 |
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US06/888,583 Expired - Lifetime US4770807A (en) | 1985-07-31 | 1986-07-21 | Novel extraction agents and novel propane diamides |
US07/203,901 Expired - Lifetime US4938871A (en) | 1985-07-31 | 1988-06-08 | Method for the recovery of actinides and/or lanthanides using novel extraction agents, and novel propane diamides, and the preparation thereof |
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US07/203,901 Expired - Lifetime US4938871A (en) | 1985-07-31 | 1988-06-08 | Method for the recovery of actinides and/or lanthanides using novel extraction agents, and novel propane diamides, and the preparation thereof |
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US (2) | US4770807A (en) |
EP (1) | EP0210928B1 (en) |
JP (1) | JPH0761990B2 (en) |
DE (1) | DE3669539D1 (en) |
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Also Published As
Publication number | Publication date |
---|---|
US4938871A (en) | 1990-07-03 |
EP0210928B1 (en) | 1990-03-14 |
DE3669539D1 (en) | 1990-04-19 |
JPH0761990B2 (en) | 1995-07-05 |
JPS6236347A (en) | 1987-02-17 |
EP0210928A1 (en) | 1987-02-04 |
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